U-69593 (BioDeep_00000646561)

   


代谢物信息卡片


n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide

化学式: C22H32N2O2 (356.24636519999996)
中文名称: (+)-(5α,7α,8β)-N-甲基-N-[7-(1-吡咯烷基)-1-氧螺[4.5]十二-8-基]-苯乙酰胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN(C1CCC2(CCCO2)CC1N3CCCC3)C(=O)CC4=CC=CC=C4
InChI: InChI=1S/C22H32N2O2/c1-23(21(25)16-18-8-3-2-4-9-18)19-10-12-22(11-7-15-26-22)17-20(19)24-13-5-6-14-24/h2-4,8-9,19-20H,5-7,10-17H2,1H3/t19-,20-,22-/m0/s1

描述信息

D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents
D045283 - Natriuretic Agents > D004232 - Diuretics
U-69593 is a potent and selective κ1-opioid receptor agonist[1]. U-69593 attenuates addictive agent-induced behavioral sensitization in the rat[2]. U-69593 reduces anxiety and enhances spontaneous alternation memory in mice[3]. U-69593 reduces calcium-dependent dialysate levels of dopamine and glutamate in the ventral striatum[4].

同义名列表

2 个代谢物同义名

n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide; U-69593



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Samuel Obeng, Shyam H Kamble, Morgan E Reeves, Luis F Restrepo, Avi Patel, Mira Behnke, Nelson J-Y Chear, Surash Ramanathan, Abhisheak Sharma, Francisco León, Takato Hiranita, Bonnie A Avery, Lance R McMahon, Christopher R McCurdy. Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids. Journal of medicinal chemistry. 2020 01; 63(1):433-439. doi: 10.1021/acs.jmedchem.9b01465. [PMID: 31834797]
  • Selena S Schattauer, Benjamin B Land, Kathryn L Reichard, Antony D Abraham, Lauren M Burgeno, Jamie R Kuhar, Paul E M Phillips, Shao En Ong, Charles Chavkin. Peroxiredoxin 6 mediates Gαi protein-coupled receptor inactivation by cJun kinase. Nature communications. 2017 09; 8(1):743. doi: 10.1038/s41467-017-00791-2. [PMID: 28963507]
  • Sascha Treskatsch, Mohammed Shaqura, Lukas Dehe, Aarne Feldheiser, Torsten K Roepke, Mehdi Shakibaei, Claudia D Spies, Michael Schäfer, Shaaban A Mousa. Upregulation of the kappa opioidergic system in left ventricular rat myocardium in response to volume overload: Adaptive changes of the cardiac kappa opioid system in heart failure. Pharmacological research. 2015 Dec; 102(?):33-41. doi: 10.1016/j.phrs.2015.09.005. [PMID: 26365878]
  • Vladimir I Chefer, Cristina M Bäckman, Eduardo D Gigante, Toni S Shippenberg. Kappa opioid receptors on dopaminergic neurons are necessary for kappa-mediated place aversion. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2013 Dec; 38(13):2623-31. doi: 10.1038/npp.2013.171. [PMID: 23921954]
  • Bing Cao, Xu Zhang, Ni Yan, Shengliang Chen, Ying Li. Cholecystokinin enhances visceral pain-related affective memory via vagal afferent pathway in rats. Molecular brain. 2012 Jun; 5(?):19. doi: 10.1186/1756-6606-5-19. [PMID: 22681758]
  • Aashish S Morani, Bronwyn Kivell, Thomas E Prisinzano, Susan Schenk. Effect of kappa-opioid receptor agonists U69593, U50488H, spiradoline and salvinorin A on cocaine-induced drug-seeking in rats. Pharmacology, biochemistry, and behavior. 2009 Dec; 94(2):244-9. doi: 10.1016/j.pbb.2009.09.002. [PMID: 19747933]
  • Lisa E Baker, John J Panos, Bryan A Killinger, Mary M Peet, Lisa M Bell, Larissa A Haliw, Sheryl L Walker. Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats. Psychopharmacology. 2009 Apr; 203(2):203-11. doi: 10.1007/s00213-008-1458-3. [PMID: 19153716]
  • Sara M Thomasy, Khursheed R Mama, Scott D Stanley. Comparison of liquid chromatography-mass spectrometry and radioimmunoassay for measurement of fentanyl and determination of pharmacokinetics in equine plasma. Journal of analytical toxicology. 2008 Nov; 32(9):754-9. doi: 10.1093/jat/32.9.754. [PMID: 19021930]
  • Elena Zakharova, Stephanie L Collins, Maria Aberg, Adarsh Kumar, J B Fernandez, Sari Izenwasser. Depletion of serotonin decreases the effects of the kappa-opioid receptor agonist U-69593 on cocaine-stimulated activity. European journal of pharmacology. 2008 May; 586(1-3):123-9. doi: 10.1016/j.ejphar.2008.02.065. [PMID: 18395712]
  • Kenneth M Wannemacher, Prem N Yadav, Richard D Howells. A select set of opioid ligands induce up-regulation by promoting the maturation and stability of the rat kappa-opioid receptor in human embryonic kidney 293 cells. The Journal of pharmacology and experimental therapeutics. 2007 Nov; 323(2):614-25. doi: 10.1124/jpet.107.125500. [PMID: 17720886]
  • Catherine B Willmore-Fordham, Daniel M Krall, Christopher R McCurdy, David H Kinder. The hallucinogen derived from Salvia divinorum, salvinorin A, has kappa-opioid agonist discriminative stimulus effects in rats. Neuropharmacology. 2007 Sep; 53(4):481-6. doi: 10.1016/j.neuropharm.2007.06.008. [PMID: 17681558]
  • Eduardo R Butelman, Marek Mandau, Kevin Tidgewell, Thomas E Prisinzano, Vadim Yuferov, Mary Jeanne Kreek. Effects of salvinorin A, a kappa-opioid hallucinogen, on a neuroendocrine biomarker assay in nonhuman primates with high kappa-receptor homology to humans. The Journal of pharmacology and experimental therapeutics. 2007 Jan; 320(1):300-6. doi: 10.1124/jpet.106.112417. [PMID: 17060493]
  • Wayne W Harding, Matthew Schmidt, Kevin Tidgewell, Pavitra Kannan, Kenneth G Holden, Brian Gilmour, Hernan Navarro, Richard B Rothman, Thomas E Prisinzano. Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A. Journal of natural products. 2006 Jan; 69(1):107-12. doi: 10.1021/np050398i. [PMID: 16441078]
  • Gavin Bart, James H Schluger, Lisa Borg, Ann Ho, Jean M Bidlack, Mary Jeanne Kreek. Nalmefene induced elevation in serum prolactin in normal human volunteers: partial kappa opioid agonist activity?. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2005 Dec; 30(12):2254-62. doi: 10.1038/sj.npp.1300811. [PMID: 15988468]
  • William E Fantegrossi, Kelly M Kugle, Leander J Valdes, Masato Koreeda, James H Woods. Kappa-opioid receptor-mediated effects of the plant-derived hallucinogen, salvinorin A, on inverted screen performance in the mouse. Behavioural pharmacology. 2005 Dec; 16(8):627-33. doi: 10.1097/00008877-200512000-00005. [PMID: 16286814]
  • E R Butelman, M C Ko, J R Traynor, J A Vivian, M J Kreek, J H Woods. GR89,696: a potent kappa-opioid agonist with subtype selectivity in rhesus monkeys. The Journal of pharmacology and experimental therapeutics. 2001 Sep; 298(3):1049-59. doi: . [PMID: 11504802]
  • S L Collins, C D'Addario, S Izenwasser. Effects of kappa-opioid receptor agonists on long-term cocaine use and dopamine neurotransmission. European journal of pharmacology. 2001 Aug; 426(1-2):25-34. doi: 10.1016/s0014-2999(01)01194-3. [PMID: 11525767]
  • S L Collins, R M Gerdes, C D'Addario, S Izenwasser. Kappa opioid agonists alter dopamine markers and cocaine-stimulated locomotor activity. Behavioural pharmacology. 2001 Jul; 12(4):237-45. doi: 10.1097/00008877-200107000-00002. [PMID: 11548109]
  • A C Thompson, A Zapata, J B Justice, R A Vaughan, L G Sharpe, T S Shippenberg. Kappa-opioid receptor activation modifies dopamine uptake in the nucleus accumbens and opposes the effects of cocaine. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2000 Dec; 20(24):9333-40. doi: 10.1523/jneurosci.20-24-09333.2000. [PMID: 11125013]
  • E Dermitzaki, E Chatzaki, A Gravanis, A N Margioris. Opioids transiently prevent activation of apoptotic mechanisms following short periods of serum withdrawal. Journal of neurochemistry. 2000 Mar; 74(3):960-9. doi: 10.1046/j.1471-4159.2000.0740960.x. [PMID: 10693926]
  • J A Vivian, M B DeYoung, T L Sumpter, J R Traynor, J W Lewis, J H Woods. kappa-Opioid receptor effects of butorphanol in rhesus monkeys. The Journal of pharmacology and experimental therapeutics. 1999 Jul; 290(1):259-65. doi: NULL. [PMID: 10381785]
  • R M Craft, P J Kruzich, J S Boyer, J W Harding, J M Hanesworth. Sex differences in discriminative stimulus and diuretic effects of the kappa opioid agonist U69,593 in the rat. Pharmacology, biochemistry, and behavior. 1998 Dec; 61(4):395-403. doi: 10.1016/s0091-3057(98)00124-5. [PMID: 9802834]
  • S Izenwasser, J B Acri, P M Kunko, T Shippenberg. Repeated treatment with the selective kappa opioid agonist U-69593 produces a marked depletion of dopamine D2 receptors. Synapse (New York, N.Y.). 1998 Nov; 30(3):275-83. doi: 10.1002/(sici)1098-2396(199811)30:3<275::aid-syn5>3.0.co;2-8. [PMID: 9776131]
  • Z J Cheng, Q M Yu, Y L Wu, L Ma, G Pei. Selective interference of beta-arrestin 1 with kappa and delta but not mu opioid receptor/G protein coupling. The Journal of biological chemistry. 1998 Sep; 273(38):24328-33. doi: 10.1074/jbc.273.38.24328. [PMID: 9733719]
  • H Kubota, R B Rothman, C Dersch, K McCullough, J Pinto, K C Rice. Synthesis and biological activity of 3-substituted 3-desoxynaltrindole derivatives. Bioorganic & medicinal chemistry letters. 1998 Apr; 8(7):799-804. doi: 10.1016/s0960-894x(98)00105-x. [PMID: 9871544]
  • S M Rawls, J F McGinty. Kappa receptor activation attenuates L-trans-pyrrolidine-2,4-dicarboxylic acid-evoked glutamate levels in the striatum. Journal of neurochemistry. 1998 Feb; 70(2):626-34. doi: 10.1046/j.1471-4159.1998.70020626.x. [PMID: 9453556]
  • M M Belcheva, Z Vogel, E Ignatova, T Avidor-Reiss, R Zippel, R Levy, E C Young, J Barg, C J Coscia. Opioid modulation of extracellular signal-regulated protein kinase activity is ras-dependent and involves Gbetagamma subunits. Journal of neurochemistry. 1998 Feb; 70(2):635-45. doi: 10.1046/j.1471-4159.1998.70020635.x. [PMID: 9453557]
  • G Dawson, S A Dawson, R Goswami. Chronic exposure to kappa-opioids enhances the susceptibility of immortalized neurons (F-11kappa 7) to apoptosis-inducing drugs by a mechanism that may involve ceramide. Journal of neurochemistry. 1997 Jun; 68(6):2363-70. doi: 10.1046/j.1471-4159.1997.68062363.x. [PMID: 9166729]
  • A D Blake, G Bot, S Li, J C Freeman, T Reisine. Differential agonist regulation of the human kappa-opioid receptor. Journal of neurochemistry. 1997 May; 68(5):1846-52. doi: 10.1046/j.1471-4159.1997.68051846.x. [PMID: 9109509]
  • C D Soulard, S Guerif, A Payne, S G Dahl. Differential effects of fedotozine compared to other kappa agonists on diuresis in rats. The Journal of pharmacology and experimental therapeutics. 1996 Dec; 279(3):1379-85. doi: . [PMID: 8968362]
  • T B van Wimersma Greidanus, S Janssen, J C Frankhuijzen-Sierevogel, C Maigret, B J van de Heijning. Effect of central administration of the kappa-opiate receptor agonist U 69.593 on neurohypophyseal hormone levels in blood and cerebrospinal fluid. Neuropeptides. 1996 Oct; 30(5):452-5. doi: 10.1016/s0143-4179(96)90009-8. [PMID: 8923507]
  • E Ronken, A H Mulder, A N Schoffelmeer. Glucocorticoid and mineralocorticoid receptors differentially modulate cultured dopaminergic neurons of rat ventral mesencephalon. European journal of pharmacology. 1994 Sep; 263(1-2):149-56. doi: 10.1016/0014-2999(94)90535-5. [PMID: 7821346]
  • L Zhang, Z F Gu, T Pradhan, R T Jensen, P N Maton. Characterization of opioid receptors on smooth muscle cells from guinea pig stomach. The American journal of physiology. 1992 Mar; 262(3 Pt 1):G461-9. doi: 10.1152/ajpgi.1992.262.3.g461. [PMID: 1312793]
  • Y Sasaki-Yagi, S Kimura, Y Imanishi. Binding to opioid receptors of enkephalin derivatives taking alpha-helical conformation and its dimer. International journal of peptide and protein research. 1991 Oct; 38(4):378-84. doi: 10.1111/j.1399-3011.1991.tb01517.x. [PMID: 1665842]
  • V U Dissanayake, J Hughes, J C Hunter. Opioid binding sites in the guinea pig and rat kidney: radioligand homogenate binding and autoradiography. Molecular pharmacology. 1991 Jul; 40(1):93-100. doi: NULL. [PMID: 1649966]
  • T S Shippenberg, A Herz. Influence of chronic lithium treatment upon the motivational effects of opioids: alteration in the effects of mu- but not kappa-opioid receptor ligands. The Journal of pharmacology and experimental therapeutics. 1991 Mar; 256(3):1101-6. doi: NULL. [PMID: 1848627]
  • B Przewłocka, A Sumová, W Lasoń. The influence of conditioned fear-induced stress on the opioid systems in the rat. Pharmacology, biochemistry, and behavior. 1990 Dec; 37(4):661-6. doi: 10.1016/0091-3057(90)90543-q. [PMID: 1982694]
  • B R de Costa, K C Rice, W D Bowen, A Thurkauf, R B Rothman, L Band, A E Jacobson, L Radesca, P C Contreras, N M Gray. Synthesis and evaluation of N-substituted cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines as high affinity sigma receptor ligands. Identification of a new class of highly potent and selective sigma receptor probes. Journal of medicinal chemistry. 1990 Nov; 33(11):3100-10. doi: 10.1021/jm00173a030. [PMID: 2172538]
  • P Zanoli, M Baraldi. Evidence that bremazocine prevents urine retention induced by intraspinal cord injection of colchicine in rats. Journal of the autonomic nervous system. 1990 Jul; 30 Suppl(?):S191-3. doi: 10.1016/0165-1838(90)90129-7. [PMID: 2170490]
  • B R de Costa, R B Rothman, V Bykov, L Band, A Pert, A E Jacobson, K C Rice. Probes for narcotic receptor mediated phenomena. 17. Synthesis and evaluation of a series of trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacet amide (U50,488) related isothiocyanate derivatives as opioid receptor affinity ligands. Journal of medicinal chemistry. 1990 Apr; 33(4):1171-6. doi: 10.1021/jm00166a014. [PMID: 2157008]
  • C N May, M R Dashwood, C J Whitehead, C J Mathias. Differential cardiovascular and respiratory responses to central administration of selective opioid agonists in conscious rabbits: correlation with receptor distribution. British journal of pharmacology. 1989 Nov; 98(3):903-13. doi: 10.1111/j.1476-5381.1989.tb14620.x. [PMID: 2556206]
  • G Bianchi. High-performance liquid chromatographic assay of k-opioid selective benzeneacetamide derivatives (U50488, U69593 and PD117302) in rat plasma and brain. Journal of chromatography. 1989 Jul; 491(2):481-7. doi: 10.1016/s0378-4347(00)82869-8. [PMID: 2553762]
  • B R de Costa, R B Rothman, V Bykov, A E Jacobson, K C Rice. Selective and enantiospecific acylation of kappa opioid receptors by (1S,2S)-trans-2-isothiocyanato-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexy l] benzeneacetamide. Demonstration of kappa receptor heterogeneity. Journal of medicinal chemistry. 1989 Feb; 32(2):281-3. doi: 10.1021/jm00122a001. [PMID: 2536435]
  • P R Oeltgen, J R Welborn, P A Nuchols, W A Spurrier, D S Bruce, T P Su. Opioids and hibernation. II. Effects of kappa opioid U69593 on induction of hibernation in summer-active ground squirrels by 'hibernation induction trigger' (HIT). Life sciences. 1987 Nov; 41(18):2115-20. doi: 10.1016/0024-3205(87)90529-7. [PMID: 2823039]